Synonym
Ligustilide A; cis-Ligustilide;
IUPAC/Chemical Name
(Z)-3-butylidene-4,5-dihydroisobenzofuran-1(3H)-one
InChi Key
IQVQXVFMNOFTMU-FLIBITNWSA-N
InChi Code
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3/b11-8-
SMILES Code
O=C1O/C(C2=C1C=CCC2)=C\CCC
Appearance
A solution in ethanol
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
(Z)-Ligustilide inhibits the expression of FATP5 and DGAT.
In vitro activity:
Importantly, Z-LIG ((Z)-Ligustilide) significantly restored the ERα protein expression in all these three ERα− breast cancer cells in both concentration and time-dependent way. (Figure 4A and 4B).These results suggest that Z-LIG significantly reactivated the transcriptional activity of ERα in ERα− breast cancer cells.
Reference: Oncotarget. 2017 Apr 25;8(17):29328-29345. https://pubmed.ncbi.nlm.nih.gov/28415616/
In vivo activity:
In vivo, rats treated intravenously with LIG (Z-ligustilide) immediately after the surgery was finished had less neurological dysfunction and smaller infarct volume than that of the vehicle-treated rats. Additionally, LIG promoted Nrf2 nuclear translocation, and further remarkably increased Nrf2 and HO-1 protein expression.
Reference: Brain Res. 2013 Jul 3;1520:168-77. https://pubmed.ncbi.nlm.nih.gov/23688544/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
1.0 |
5.26 |
|
| DMSO |
50.5 |
265.45 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
190.24
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Ma H, Li L, Dou G, Wang C, Li J, He H, Wu M, Qi H. Z-ligustilide restores tamoxifen sensitivity of ERa negative breast cancer cells by reversing MTA1/IFI16/HDACs complex mediated epigenetic repression of ERa. Oncotarget. 2017 Apr 25;8(17):29328-29345. doi: 10.18632/oncotarget.16440. PMID: 28415616; PMCID: PMC5438733.
2. Qi H, Jiang Z, Wang C, Yang Y, Li L, He H, Yu Z. Sensitization of tamoxifen-resistant breast cancer cells by Z-ligustilide through inhibiting autophagy and accumulating DNA damages. Oncotarget. 2017 Apr 25;8(17):29300-29317. doi: 10.18632/oncotarget.16832. PMID: 28431397; PMCID: PMC5438731.
3. Ma JC, Zhang HL, Huang HP, Ma ZL, Chen SF, Qiu ZK, Chen JS. Antidepressant-like effects of Z-ligustilide on chronic unpredictable mild stress-induced depression in rats. Exp Ther Med. 2021 Jul;22(1):677. doi: 10.3892/etm.2021.10109. Epub 2021 Apr 25. PMID: 33986842; PMCID: PMC8112151.
4. Peng B, Zhao P, Lu YP, Chen MM, Sun H, Wu XM, Zhu L. Z-ligustilide activates the Nrf2/HO-1 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. Brain Res. 2013 Jul 3;1520:168-77. doi: 10.1016/j.brainres.2013.05.009. Epub 2013 May 18. PMID: 23688544.
In vitro protocol:
1. Ma H, Li L, Dou G, Wang C, Li J, He H, Wu M, Qi H. Z-ligustilide restores tamoxifen sensitivity of ERa negative breast cancer cells by reversing MTA1/IFI16/HDACs complex mediated epigenetic repression of ERa. Oncotarget. 2017 Apr 25;8(17):29328-29345. doi: 10.18632/oncotarget.16440. PMID: 28415616; PMCID: PMC5438733.
2. Qi H, Jiang Z, Wang C, Yang Y, Li L, He H, Yu Z. Sensitization of tamoxifen-resistant breast cancer cells by Z-ligustilide through inhibiting autophagy and accumulating DNA damages. Oncotarget. 2017 Apr 25;8(17):29300-29317. doi: 10.18632/oncotarget.16832. PMID: 28431397; PMCID: PMC5438731.
In vivo protocol:
1. Ma JC, Zhang HL, Huang HP, Ma ZL, Chen SF, Qiu ZK, Chen JS. Antidepressant-like effects of Z-ligustilide on chronic unpredictable mild stress-induced depression in rats. Exp Ther Med. 2021 Jul;22(1):677. doi: 10.3892/etm.2021.10109. Epub 2021 Apr 25. PMID: 33986842; PMCID: PMC8112151.
2. Peng B, Zhao P, Lu YP, Chen MM, Sun H, Wu XM, Zhu L. Z-ligustilide activates the Nrf2/HO-1 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. Brain Res. 2013 Jul 3;1520:168-77. doi: 10.1016/j.brainres.2013.05.009. Epub 2013 May 18. PMID: 23688544.
1. Gijbels, M.J.M., Fischer, F.C., Scheffer, J.J.C., et al. Phthalides in roots of Anethum graveolens and Todaroa montana. Scientia Pharmaceutica 51(4), 414-417 (1983).
2. Qi, H., Jiang, Z., Wang, C., et al. Sensitization of tamoxifen-resistant breast cancer cells by Z-ligustilide through inhibiting autophagy and accumulating DNA damages. Oncotarget 8(17), 29300-29317 (2017).
3. Wang, Y.-R., Xu, H., Tao, M., et al. Ligustilide relieves complete Freund’s adjuvant-induced mechanical hyperalgesia through inhibiting the activation of spinal c-Jun N-terminal kinase/c-Jun pathway in rats. Pharmacogn. Mag. 13(52), 634-638 (2017).
4. Xiao, W., Yu, A., Liu, D., et al. Ligustilide treatment promotes functional recovery in a rat model of spinal cord injury via preventing ROS production. Int. J. Clin. Exp. Pathol. 8(10), 12005-12013 (2015).
5. Peng, B., Zhao, P., Lu, Y.-P., et al. Z-ligustilide activates the Nrf2/HO-1 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro. Brain Res. 1520, 168-177 (2013).
